HCID 21950315, compound → HCID 67539782, compound

HRID 1192399Notes

Reaction equation

[ClH:1].Cl.[CH:3]1([C:6]2[C:7]([NH2:18])=[N:8][CH:9]=[N:10][C:11]=2[N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH2:5][CH2:4]1.C(OC([NH:26][CH2:27][CH2:28][CH:29]([C:33]1[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=1)[C:30](O)=[O:31])=O)(C)(C)C>>[ClH:39].[ClH:1].[NH2:26][CH2:27][CH2:28][CH:29]([C:33]1[CH:34]=[CH:35][C:36]([Cl:39])=[CH:37][CH:38]=1)[C:30]([N:15]1[CH2:16][CH2:17][N:12]([C:11]2[C:6]([CH:3]3[CH2:5][CH2:4]3)=[C:7]([NH2:18])[N:8]=[CH:9][N:10]=2)[CH2:13][CH2:14]1)=[O:31]

Participants

Reactant 2

HCID 21950315HCID 21950315, compound

HCID 67539734HCID 67539734, compound

Product 1

HCID 67539782HCID 67539782, compound

Procedure

4-Amino-1-[4-(6-amino-5-cyclopropyl-pyrimidin-4-yl)-piperazin-1-yl]-2-(4-chlorophenyl)-butan-1-one dihydrochloride was prepared by substituting 5-piperazin-1-yl-1H-indazole with 5-Cyclopropyl-6-piperazin-1-yl-pyrimidin-4-ylamine dihydrochloride and substituting (D)-Boc-4-chlorophenylalanine with 4-tert-Butoxycarbonylarnino-2-(4-chlorophenyl)-butyric acid in Example 34, Step 2, then removing the Boc protecting group as described in Example 34, Step 3. 1H NMR (CD3OD, 400 MHz) δ 8.04 (s, 1H), 7.41 (d, J=8.4 Hz, 2H), 7.33 (d, J=8.4 Hz, 2H), 4.19 (m, 1H), 3.95 (m, 1H), 3.85 (m, 2H), 3.61 (m, 3H), 3.22 (m, 2H), 2.95 (m, 1H), 2.82 (m, 1H), 2.31 (m, 1H), 2.01 (m, 1H), 1.56 (m, 1H), 1.08 (m, 2H), 0.47 (m, 2H). LCMS (APCI+) m/z 415, 417 [M+H]+; Rt=1.87 min.

Workup

customremoving the Boc protecting group

Sources & evidence

ORD record: ord-442e2a8514e746779ef27a82177f8e81
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680114B2

Reaction notes

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